


Unlikely Savior

by songofhell



Category: Supernatural
Genre: M/M, Season 4 AU, mentions of torture
Language: English
Status: Completed
Published: 2017-06-09
Updated: 2017-06-10
Packaged: 2018-11-12 03:05:10
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 8
Words: 11,515
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11152917
Author URL: https://archiveofourown.org/users/songofhell/pseuds/songofhell
Summary: Dean never expected to get out of Hell, but if the thought had occurred to him, he would definitely have never imagined his rescue at the hands of a demon. Crowley claims that he wants to stop Lilith just as much as the Winchesters, but then again, so does Ruby. The brothers need to decide which demon to trust - or if they should trust either.





	1. Rescue

“Well. You certainly look like you’re having fun.”

Normally, Dean ignored the words spoken to him while he was torturing the other unfortunate souls in Hell. But that voice wasn’t Alastair’s. He released his grip on the knife, leaving it where it stuck beneath the layer of flesh on the man’s chest, and turned around to face the demon behind him.

Most of his interactions in Hell were limited to Alastair, but he had still met a small handful of other demons. This was not one of them. This demon looked out of place amongst the blood, chains, and instruments of torture; with the immaculate suit he was wearing, he would have looked much more at home behind a desk in a prestigious office building. But there was a look in his eyes that Dean had come to recognize, a look that told of enjoyment at the pain around him, a look that said he would pick up a knife without a second thought and start carving into some pour soul’s flesh. It was the same look in Dean’s eyes as he met his gaze. “And who are you?”

“The name’s Crowley. I’ve come to get you out of here.”

“What do you-?” That was all he managed to get out before the scene before him abruptly vanished, his stomach clenching as everything spun around him, disorienting him. He became aware of the fact that he was no longer standing, but was lying down on a hard, uncomfortable surface. He felt around with his hands for a few seconds, before pulling a lighter out of his pocket and lighting it up. As soon as his eyes adjusted, he knew where he was… a coffin.

He tried calling for help, but his throat was so dry, he could hardly hear himself. Some part of him wondered if he was back to being tortured, if maybe the demons in Hell were getting creative. But it didn’t feel right. Hell had a distinct feeling to it, and the current atmosphere, while far from pleasant, was distinctly lacking that feeling. So, he was out. And he was buried alive.

He pushed against the wood of the lid of the coffin, managing to break through, and then started digging up, hoping that he didn’t suffocate before he managed to get to the surface. Relief coursed through him as his hand slid through the dirt to feel nothing above it, but it was even sweeter when he pulled his head up and took a deep breath of air. He pulled himself out of the grave, ignoring the pain that was shooting through his body, not stopping until his feet breached the surface and he rolled onto his back, just breathing. He was alive.

Suddenly, a shadow fell over him. He pushed himself up to see the same demon from Hell – Crowley – standing behind him.

“Well done,” Crowley said, holding out a bottle of water to him. “You look like you could use a drink.”

Dean was wary, but he was also freaking thirsty, so he took the water, chugging it all at once. “You could’ve helped,” he muttered hoarsely when he was done.

He scoffed. “I _did_ help. I got you out of Hell – that was the hard part. You can’t expect me to do everything for you.”

Dean narrowed his eyes as he got to his feet. “Why did you get me out of Hell?”

“All in good time,” he promised with a smile. “First, you need a shower.” He snapped his fingers, and then they were standing in a hotel room far nicer than anything Dean had stayed in before. “Now, you go get washed up, and room service should be here by the time you finish up.”

“Why-”

“You do want to eat, yes?”

Dean nodded.

“Then take a shower, and food will be waiting for you when you’re done.”

He still didn’t move, so Crowley sighed, flicking his hand in Dean’s direction. Suddenly, Dean was flying into the bathroom, the door slamming shut behind him. Taking the hint that it was probably best to just do as he was told, and not having it in him to put up a fight at the moment, he got in the shower.

Honestly, it felt good. The warm water washed over his muscles, soothing them. But at the same time, the shower allowed for too much freedom of thought. And he didn’t want to think right now. Not after everything that had just happened, everything that he had done. So, he took as little time as possible before he hastily dried himself off and pulled on the clothes that had been folded neatly on the toilet. He assumed they were meant for him, as they were his size – they were a bit nicer than anything he normally wore, but still casual enough to be comfortable.

“What year is it?” he asked as he walked back out to the main room of the suite. It felt like decades that he had been in Hell. Was Sam even still alive?

“It’s the same year you died – just four months later.” Crowley removed the lid from the tray that was on the coffee table and took a seat on the couch, patting the cushion beside him to indicate that Dean should join him.

“Just four months?” he asked slowly as he walked around and sat down on the couch. “But it felt like…”

“Forty years,” he nodded. “Time passes differently in Hell.” He motioned to the tray of food, and Dean didn’t need telling twice. He could feel Crowley watching him as he dug in, but at the moment, he couldn’t bring himself to care.

“You ever going to tell me what the point of this is?” he asked eventually.

Crowley eyed him thoughtfully for a second, before asking, “You ever wonder why that crossroads demon let you make that deal? After she told you that she wasn’t supposed to?”

Dean blinked in surprise. “I figured it was cause I was desperate, and she knew I’d agree to anything.”

“Well, that helped. But no. It was because Lilith wanted you, Dean. She _needed_ you to make that deal. The demon only claimed that she was breaking the rules to get your years down, so that Lilith would get what she wanted that much sooner.”

“Why?” he demanded. “What did she want with me?”

“She intends to break 66 seals in order to free Lucifer himself – and the first seal was for the righteous man to shed blood in Hell – the righteous man being you.”

Dean’s mind took a few seconds to play catch-up. “Wait. _Lucifer_ Lucifer? As in, the devil?”

“If anyone else has the name, that is truly unfortunate.”

“He’s real?”

“Oh, yes.”

It felt as though a weight had just settled on his stomach. “And I broke the first seal.”

“Yes… I had been hoping that I would get to you _before_ you did that.”

Dean looked at him in confusion. “Wait, so you _don’t_ want Lucifer to be free?”

“No,” he said simply, as though that should be obvious.

His eyebrows furrowed further. “But you’re a demon.”

He raised his eyebrows slightly as he nodded. “Yes.”

“Don’t you… I mean, didn’t he create you? Aren’t you supposed to worship him?”

“According to him, sure. But to him, we're just servants. Cannon fodder. If Lucifer manages to exterminate humankind, we're next.”

Dean eyed the demon through narrowed eyes, unsure if he was buying his story. But without knowing why he was really here, it was difficult to judge what Crowley might stand to gain by lying. “So… not that I’m not glad to be out of Hell, but what was the point of rescuing me if the seal is already broken?”

“I should think that would be obvious.”

“Well, it ain’t.”

Crowley sighed. “What exactly do you intend to do with this information I have given you?”

Dean thought about it for a couple seconds. “Try to kill Lilith before she can break anymore seals.”

He smirked. “See? Our goals are the same, Dean. Why not work together to achieve them?”

“Oh, I don’t know? Because you’re a demon.”

He rolled his eyes. “Would you really rather risk Lucifer being freed than work with a demon? Besides, you were nearly one yourself, before I pulled you out.”

He felt sick at the thought, so he pushed it away, eyeing Crowley suspiciously. “How do I know you’re even telling the truth?”

“What could I possibly gain from this? I rescued a soul from Hell – if you think embezzlement on Earth is bad, it has nothing on when the company you work for is Hell. And of course, I didn’t steal just any soul – I stole their most prized soul. If they find out that it was me, you can’t even… well, _you_ might actually be able to imagine what they’ll do to me. And on top of that, I’m suggesting we go up against the demon currently in charge. That is not something I would risk unless I was bound and determine to prevent Lucifer’s release.”

Dean tried to think of some other reason why Crowley might have rescued him from Hell, why he would want him to take down Lilith, but he couldn’t come up with anything. Dean doubted that he would go through the all the effort of springing him if he just wanted her dead for personal reasons. Even if that was the case, though; it didn’t change the fact that Dean wanted her dead, too.

“Alright, so what are the seals?”

“Not sure.”

“You’re not sure?” Dean repeated in disbelief.

“Well, I know _some_ of them. But there are over 600 possibilities – there’s no telling what she’ll do.”

He sighed. “Great. So, what’s your plan, then?”

“I gather intel and pass it along to you, until you are able to take her out.”

“That’s it? That’s all you got?”

“Well, my original plan had been to prevent the first seal from being broken at all – if it were to remain unbroken, Lilith would be unable to break any others. But that didn’t exactly work out, now, did it?”

Dean recoiled as though he had been hit. If Lilith managed to free Lucifer, it was on him. He had broken the first seal, he had started this. And now he had to stop it.


	2. Reunion

Crowley insisted that Dean get some sleep before he did anything else, so it wasn’t until the next morning that he went to Bobby’s. The greeting he got wasn’t exactly welcoming, but Bobby had a right to be suspicious. Finally, he seemed to realize that the man in front of him really was Dean, and he pulled him into a hug.

“It’s… it’s good to see you, boy,” he muttered as he pulled back.

“Yeah, you two,” Dean sighed.

“But… how did you bust out?”

“Uh… that’s a bit of a story, really.  There’s this-” He was interrupted by a face full of holy water. He grimaced, spitting out the water. “I’m not a demon either, you know.”

“Sorry. Can’t be too careful. You were sayin’?”

He grabbed a towel to wipe off his face. “A demon pulled me out of Hell,” he muttered.

“What?” Bobby looked at him incredulously.

“Yeah.” Dean nodded sympathetically. “Surprised me, too.” He nodded towards the study, and Bobby turned to walk into it, Dean following behind him.

“But why would a demon pull you out?”

“Because he wants me to save the world, apparently.”

“But… that don’t make a lick of sense,” Bobby muttered as he moved to stand behind his desk, and Dean faced him across it.

“Yeah. Yeah, you're preachin' to the choir. But Crowley said that Lilith is trying to free Lucifer, and he wants me to stop her.”

His eyes grew wide. _“Lucifer?”_

“Yep.”

“And this Crowley doesn’t want him freed?”

“No. He says that after Lucifer wipes out humans, demons will be next.”

“And do you believe him?”

“I don’t know what to believe,” Dean sighed. “I can’t see why he would be lying, but he is a demon.” He shook his head. “Where’s Sam, anyway?”

Bobby hesitated. “I don’t know.”

“You don’t know?” he demanded. “What do you mean, you don’t know?”

“I haven't talked to him for months,” he admitted.

“You're kidding, you just let him go off by himself?”

“He was dead set on it.”

“Bobby, you should've been looking after him.”

“I tried. These last months haven't been exactly easy, you know. For him or me. We had to bury you.”

Dean’s eyebrows drew together slightly. “Why did you bury me, anyway?”

“I wanted you salted and burned. Usual drill,” Bobby explained. “But... Sam wouldn't have it.”

“Well, I'm glad he won that one,” he muttered, vaguely wondering what would have happened if his body had been salted and burned.

“He said you'd need a body when he got you back home somehow. That's about all he said.”

He frowned, the gears in his head spinning. “What do you mean?”

“He was quiet. Real quiet,” Bobby muttered as he sat down. “And then he just took off. Wouldn't return my calls. I tried to find him, but he didn't want to be found.”

Dean sighed, running a hand over his face. “That doesn’t make any sense. If he did make a deal to get me out, why would Crowley make up this whole story about Lilith freeing Lucifer?”

Bobby shrugged. “Maybe it was part of the deal? So that you wouldn’t find out. You think he did it?”

“It’s what I would’ve done.”

Dean didn’t know what to think. His brother making a deal to get him out of Hell sure made a hell of a lot more sense than a benevolent demon, though. It was easy enough for him to track down where Sam was staying, and then he and Bobby went to see him.

Sam didn’t react much differently to seeing him than Bobby had, but thankfully Bobby was able to calm him down. Not that things didn’t get heated again when Dean accused him of making a deal.

“I tried everything,” Sam spat, pushed Dean’s hands off of him. “That's the truth. I tried opening the Devil's Gate. Hell, I tried to bargain, Dean, but no demon would deal, all right? You were rotting in Hell for months. For months, and I couldn't stop it. So, I'm sorry it wasn't me, all right?” He looked down, his voice going softer. “Dean, I'm sorry.”

Dean’s eyes grew wide as he looked at his brother, seeing the guilt that was weighing him down at the fact that he hadn’t been able to save him. “It’s okay, Sammy,” he said softly. “You don’t have to apologize, I believe you.”

Sam nodded, still not quite looking at Dean.

“So, now what’re we thinking?” Bobby asked, looking at Dean. “That the demon was telling the truth?”

At that, Sam looked up. “What demon?”

“The demon that sprang me,” Dean sighed, sitting down on the coffee table. “Crowley. He said that Lilith needs to break 66 out of 600 seals to free – wait for it – Lucifer.”

Sam’s eyes grew wide. “What?” he gasped.

“Yeah. And he supposedly pulled me out of Hell to stop her.”

He looked at him curiously. “Do you believe him?”

“He’s a demon. He’s got to be playing some kind of angle, I just don’t know what.”

“Right,” he muttered, looking away. “Anyone want a beer?”

“Hell yeah,” Dean muttered.

“Yeah, I’ll take one,” Bobby said as he sat down on the couch.

Sam nodded then when to the fridge, pulling out three beers and passing them out. “You know, I’ve been hunting down Lilith,” he said as he sat down on the edge of the bed. “Ever since I figured out I couldn’t save you… I wanted some payback.”

“All by yourself,” Bobby accused. “Who do you think you are, your old man?”

“Uh, yeah, I'm sorry, Bobby. I should have called. I was pretty messed up.”

Dean frowned as something pink on the bed beside Sam caught his eye. He walked over and picked up the pink, flowery bra which probably belonged to the girl who had left when Dean and Bobby had shown up. “Oh yeah. I really feel your pain.”

Sam cringed slightly, trying to laugh it off as Dean sat down beside him. “Anyways, whether or not this Crowley is telling the truth, I figure it’s still in our best interests to kill her.”

“I agree. But you’re not going it alone anymore.”

“’Course not.”

“Great. So, let’s kill the bitch.”


	3. Reliance

Dean decided that it would be for the best to focus on working with Sam to kill Lilith, and just forget about everything else Crowley had said to him. Who knew how much of it was true? Probably nothing, aside from the fact that Lilith needed to die. So, they could deal with Crowley once she was out of the picture.

Except… well, he had just had a really weird day, even by his standards. He, Sam, and Bobby had gone up against the ghosts of people they had failed to save. A little research showed that it was what was known as “the rising of the witnesses” – a sign of the apocalypse. And Dean couldn’t help but wonder if this was one of the seals Crowley had been talking about.

Sure enough, he woke up that night to see Crowley standing in Bobby’s kitchen, his gaze fixed on him. He sighed and got to his feet. After checking to make sure Sam was still asleep, he walked over to the demon.

“This was a seal, wasn’t it?” he muttered.

“I’m afraid so.” He stood with his hands in his pockets, his expression unreadable.

“But we stopped it. We put those spirits back to rest.”

Crowley shrugged. “All you achieved with that was saving your necks. Not that I’m not glad you did – I would hate to have gone through all the trouble of saving you for you to die now – but the seal was still broken.”

“Great,” Dean sighed. “I thought you were supposed to be digging up information for us – giving us the lowdown on what seal Lilith’s going after _before_ she breaks it.”

His gaze turned cool. “I don’t work for you, Dean – other way around, actually.”

“What the hell is _that_ supposed to mean?” he demanded hotly.

“I pulled you out of Hell to do a job, and I expect that job to be done.”

Dean scoffed, shaking his head. “You really want Lilith dead, don’t you? Why don’t you tell me what the real reason is?”

“I did tell you. I do not want Lucifer freed – it is better for everyone if he stays locked up.”

“Yeah, I ain’t buying that.”

“Then, I don’t know what you want me to say. And I don’t care.” He took a step forward. “I am trying to get information, but there is only so much I can stick my neck out without drawing attention. Seals are being broken – you can see that now. There is no telling how much time we have. So, show some initiative, would you? _Take. Her. Out.”_

Dean was unfazed. “Well, it sure would be nice if I had a way to do that, wouldn’t it? I mean, sure, we have a knife that could do the trick, but with how strong she is-”

“It would be nearly impossible to kill her with a knife, even one designed to kill demons,” Crowley finished. “You’d have to hit a vital organ, and she won’t let you do that so easily.”

“So, how the hell am I supposed to kill her, then?”

He smirked. “This should do the trick.” He reached into his coat and pulled out a gun that Dean immediately recognized – the Colt.

Dean’s breath left him in a huff. “How did you get that?”

“Doesn’t matter. All that matters is that I have it, and I’m giving it to you.” He held the gun out to him, and Dean started to reach for it, but then he stopped himself.

“What’s the catch?” he asked suspiciously.

“No catch, Dean. Just do the job that I brought you here to do.”

He hesitated just a second longer before reaching out and taking it, breathing a sigh of relief at having it in his hand again.

“I’ll be in touch,” Crowley said, then vanished from the spot.

Okay, so maybe Crowley was telling the truth about Lilith and the seals. And he had given him the Colt, so maybe he was being honest about his goals, too. An honest demon… maybe the world really was coming to an end.

The next morning, Dean told Sam about what had happened.

“And he just gave you the Colt, no strings attached?” Sam asked in disbelief.

“Yeah,” Dean sighed. “I don’t know, man. I’m starting to think he might be telling the truth.”

He raised his eyebrows slightly. “Really?”

“Yeah. I mean, what else could he be gaining from this?

“I don’t know,” he admitted with a slight frown.

“Well, something’s bothering you. What?”

“It’s just… before, with Ruby…. She helped us out a lot, and you were dead set against trusting her. But now Crowley shows up, and you’re just taking him at his word?”

“Ruby was leading you somewhere you shouldn’t have been going. And Crowley… I don’t know. I keep looking for an ulterior motive with him, but I can’t find one. That only leaves one option – he’s being honest.”

“Yeah, maybe. But… don’t take this the wrong way, but why did he never try and recruit me, instead of going through all the work of pulling you out of Hell? I mean, it’s not exactly a secret that I’ve been tracking down Lilith for the past few months. Surely that would’ve been easier – unless he needed you for something else.”

“Because…” Dean sighed. He’d been avoiding talking about what had happened in Hell, about him breaking the first seal. But it was the only answer he could give Sam, and if it helped him to trust Crowley, too, then he had to tell him. “Because that’s not the only reason he pulled me out.”

Sam’s eyebrows furrowed. “What do you mean?”

He looked down. “The seals… unless the first seal is broken, none of the others can be. And the first seal…” He took a deep breath. “The first seal was for the righteous man to shed blood in Hell… and apparently, the righteous man was me.” He could feel tears forming in his eyes as he looked back up at his brother. “He was trying to get me out before I broke the first seal. And he failed.”

“Dean,” Sam breathed, clearly not knowing what to say.

Dean looked away again. “I-I tried, Sam. But… it wasn’t just four months to me. Time’s different down there. It was more like forty years.”

It took Sam a few seconds to respond. “My god,” he muttered, horror in his voice.

And now that Dean was talking about Hell, he found it all just coming out. “They, uh... they sliced and carved and tore at me in ways that you... until there was nothing left. And then, suddenly... I would be whole again... like magic... just so they could start in all over. And this demon, Alastair... at the end of every day... every one... he would come over. And he would make me an offer. To take me off the rack... if I put souls on... if I started the torturing…. And every day, I told him to stick it where the sun shines. For 30 years, I told him. But then I couldn't do it anymore, Sammy.” His tears were becoming audible now, and there was nothing he could do to stop it. “I couldn't. And I got off that rack. God help me, I got right off it, and I started ripping them apart…. I lost count of how many souls…. The – the things that I did to them.” He took a deep breath. “And the Crowley showed up. He got me out, and I was faced with everything I had done…. And not just that, but the fact that I had broken the first seal… that if Lucifer gets out, it’s on me.”

“Dean…” Sam cleared his throat. “Dean, look, you held out for 30 years. That's longer than anyone would have.”

He raised a hand to wipe the tears from his face. “Doesn’t matter. The seals are being broken, and it’s my fault. And that’s why… I have to work with Crowley. I have to fix this.”

Sam nodded. “We will, Dean. We will.”


	4. Rendezvous

Getting a lead on Lilith was easier said than done. Sam and Dean searched, and Crowley pointed them in the direction of a few seals he thought were being targeted, but he had no information to lead them to Lilith herself. So, they passed their time with other cases that came up, while the rest of their time was devoted to searching for Lilith.

They were between cases, at the moment, and Dean was sleeping restlessly in a motel, when a sharp voice woke him. “Dean, wake up.”

Dean sprang upright, reaching under his pillow for his gun, which he aimed at the head of the man standing over him. “Crowley?” He blinked when he recognized him, lowering the gun. “It’s been weeks, man. Where the hell have you been?”

“Not the question you should be asking.” He nodded towards the other bed in the room. “Your brother often go out in the middle of the night?”

Dean looked over at Sam’s bed, which, sure enough, was empty. “Sometimes,” he admitted. “He’s been restless lately…. Why?” he asked suspiciously as he turned back to the demon.

“Because demons gossip. And the rumors that have been circulating about Samantha are… disturbing.”

He got to his feet. “What do you mean?” he demanded.

“He’s having illicit relations with a little demon by the name of Ruby, and is apparently now able to exorcise demons with his mind.”

Dean’s jaw clenched, his eyes narrowing in anger. “He told me Ruby was dead.”

“Oh, no. My sources tell me she’s very much alive and has your brother wrapped around her finger.”

 _“Dammit._ What’s she playing at, do you know?”

“No. But the fact that Lilith is letting her walk around topside after her overt betrayal is… surprising, to say the least.”

“You think she’s working with Lilith?”

“I wouldn’t be surprised. Though, what exactly her end game is, I don’t know.”

Dean shook his head, running a hand over his face. As if things weren’t bad enough…. And Sam had promised him that he wouldn’t go down this road. “Do you know where they are?”

“No. I can slip a tracking device on him in the near future, though, if you’d like.”

He looked thoughtful. “Depending on how things go when he gets back, I just might take you up on that.”

“Excellent. Well, that’s all I came to say-”

“Wait,” he cut him off. “You aren’t staying?”

Crowley frowned. “Why would I?”

“To help me out. You’ll be able to get a better read on Ruby that I will.”

“Yes, but if she _is_ working for Lilith, I would rather she not see that I’m helping you.”

“Well, I’ve got news for you – Sam might’ve already told her. It might be best if you stay and find out for yourself.”

Crowley ground his teeth together irritably. “I hope you realize that if I think there’s even a chance she’ll report me to Lilith, I can no longer get information for you.”

“Well, it’s better to know, isn’t it? It’s a chance we have to take.”

Crowley sighed and sat down on the bed. _“Fine._ So, what do you propose we do to pass the time?”

Dean shrugged as he sat down beside him. “Watch something?”

“We have very different ideas of a good time.”

“Hey, my idea of a good time is drinking and getting laid, but I can’t do that when I’m waiting for Sam to get back.”

“Well, we can drink.” Crowley snapped his fingers, and then he was holding a bottle of Scotch and two glasses. He set the glasses down on the bedside table, and poured one for the both of them, before setting the bottle down and passing one glass to Dean. “Cheers.” He raised his own glass to Dean slightly before taking a drink.

Dean took a sip of his glass and hummed contentedly. “That’s good.”

“Of course. I don’t settle for second-best.”

He snorted. “Then, why’d you choose me to help you take out Lilith?” he teased.

Crowley arched an eyebrow at him. “Because I’ve looked into the other hunters in the world, and you _are_ the best.”

He shook his head slightly, taking another drink. “Nah, I’m sure there’s better out there than me.”

“No. You and your brother are widely considered to be the most dangerous hunters out there by almost every breed of monster. But personally, I like you better. So, even once I realized it was too late to prevent the first seal from breaking, it was still you that I wanted.”

Dean blinked at him in surprise. “Why?”

Crowley eyed him appraisingly over the rim of his glass. “I’m not entirely sure…. But I see something in you, Dean – something special. Maybe it’s that delicate balance inside you – the righteousness, the self-hatred, the compassion, the darkness…. Does it ever get tiring? Trying to suppress the parts you don’t like?”

“Shut up,” he muttered, turning away.

“I’m just calling it as I see it. It certainly takes considerable strength… it’s impressive, everything you manage to lock away.”

“It’s still there, though,” he said, his voice little more than a whisper. “You can still see it.”

“Only because I caught a glimpse. I’m sure you still look as strong as ever to your little brother. Because that’s all you really care about, isn’t it?”

Dean nodded, his eyes trained on a spot on the far wall.

Crowley sighed. “I’m sure it’s admirable how much you’d do for him, but you should really think about taking care of yourself on occasion.”

“I’m fine,” he muttered.

He snorted. “Who are you trying to fool? Anyone with eyes can see how much you’re suffering. It’s only natural with what you came out of.”

“Yeah, well, Lilith’s still out there, trying to free Lucifer, and Sam’s going down a path that could lead him to god knows what. So, I don’t have much energy left for taking care of myself, at the moment.”

“Well, you should find some. Because you’re going to be useless if you’re just a shell when you go up against Lilith.”

“I’ll manage.”

“What if you don’t?” Crowley demanded, his voice firm. “What if you get yourself killed, and Sam’s too far gone, and there is no one left to protect the world? What then?”

Dean slowly turned to meet his eyes. “Then, I guess you’ll have to do it.”

His eyebrows shot up. “Excuse me?”

“You’re asking, so that means you care. Which means that, if I die, you’ll have to just stomach your demonic ego and kill Lilith yourself.”

“The backlash I would get would be-”

“Will it really matter if it’s between that and Lucifer getting free?”

He hesitated before he sighed. “No. It won’t.”

“Good. The world will be fine, then.”

Crowley eyed him curiously for several seconds. “You really trust me to save the world?”

Dean took a second to consider that. “Yeah,” he nodded. “Yeah, I do.”

“Well… I appreciate the vote of confidence, but I’d still rather it not come to that.”

“I’ll do my best not to die,” he promised.

“Good.” Crowley started to turn away, but Dean stopped him with a hand on his arm.

“But if I do,” he continued. “Promise me that you’ll do whatever you can to save Sam.”

“Dean…”

“Please. I know Bobby will help, too, but I’d feel better if he wasn’t alone.”

“I’m sure he will be able to handle things just fine.” He tried to pull away, but Dean just gripped tighter.

“What if he can’t? What if it takes a demon to know what’s going on with Sam and how to fix him?”

“Then Bobby will have to be resourceful. I can’t make that promise, Dean – I’ll have enough to worry about without trying to bring your precious Sammy back to the light.”

Dean ground his teeth together, thinking fast. Because whatever was happening to Sam was demonic in origin, and while he knew how resourceful Bobby could be, he was sure the Crowley would have a better shot of figuring out what was going on. “Okay, what about a deal, then?”

Crowley’s expression was pure disbelief. “You cannot be serious.”

“Whatever you want, and in return, if I die, you do _everything you can_ to save Sam.”

He sighed, shaking his head. “You’re offering to make a deal with a demon over something that might not even be necessary.”

“Yeah, and I hope it isn’t. But if it does come down to me dying, I won’t exactly have a chance to make the deal in the seconds before I go.”

Crowley looked at him for several seconds, his gaze calculating. “Fine,” he finally said. “You protect me from any demons, or anything else that Lilith might send after me, or that may choose to target me after we have defeated her – if you should survive that encounter. And in return, should you not survive, I will do everything in my power to get your moose back on the straight and narrow.”

Dean nodded. Sounded fair enough. “Deal.”

When Crowley started to lean in, it took Dean a second to realize what was happening. Right, sealing a demon deal was done through a kiss. He swallowed thickly as he closed his eyes and allowed his lips to slide against Crowley’s. He wasn’t entirely surprised that the sensation was pleasant – he found Crowley attractive, after all – hell, he had even been enjoying his company – so it wasn’t so much of a stretch that he would enjoy kissing him.

Crowley didn’t stop with a mere brush of the lips, though; he worked Dean’s mouth open, allowing his tongue to slip inside. Somewhere along the line, his hand had twisted in Dean’s hair, and Dean’s hand had slid up his arm to grip his shoulder. Crowley nipped lightly at Dean’s bottom lip, eliciting a soft moan from him, and he was about to lean in for more when Crowley pulled away.

Dean blinked at him in confusion, and the demon chuckled. “Not that I don’t enjoy your enthusiasm, but I just heard a car pull into the parking lot. If you would like to catch Ruby before she drives away, now is your chance.”

“Uh… right.” Dean cleared his throat as he got to his feet, trying to clear his mind of that kiss. He needed to focus on his brother right now, he could worry about what the hell had just happened between him and Crowley later.


	5. Row

Dean stepped out of the motel room as the car came to a stop in front of their door and Sam started to get out.

“Heya, Sam,” Dean called as he walked towards him, his anger an undercurrent in his voice. He ducked his head to look at the woman in the driver’s seat – the same woman from Sam’s motel room when Dean had gotten back from Hell. “Ruby.”

She gave him a small, tentative smile. “It’s good to see you again, Dean.”

Dean’s gaze went back to his brother, who was frozen in place, his eyes wide. “Dean, I can explain.”

“Oh, I hope so. Cause things aren’t looking too good for you, right now.”

He opened his mouth and closed it again, then turned back to the car. “Ruby, why don’t you go-”

“I think she should stay,” Dean interrupted, fixing her with a glare. “Come inside, have a _chat.”_

“Dean, lay off,” Sam protested, reaching out as if to hold him off from Ruby.

“I can handle myself, Sam,” Ruby said calmly. She pulled the car into a parking space and got out, walking over to stand beside Sam. “I’m not your enemy, Dean.”

“Yeah, we’ll see about that.” He spun on his heels and walked back into the room.

“How did you even find out I was with her?” Sam asked as they followed him.

He didn’t say anything, just nodded to where Crowley was sitting on the edge of the bed.

“Hello, Sam,” Crowley greeted him. “We haven’t had the pleasure of meeting yet.”

“You’re Crowley,” Sam guessed, his eyes narrowing.

“Wait… _Crowley_ is the demon who sprang your brother?” Ruby demanded, looking between Crowley and the Winchesters with wide eyes.

“Yeah, why?” he turned to her with a worried frown.

“Sam, he’s Lilith’s right-hand man!”

 _“What?”_ Sam snapped, advancing a step towards Crowley, while Dean turned to look at him with wide eyes.

Ruby had to be lying, right? She was trying to turn them against Crowley because he was who could discredit her.

Crowley rose to his feet, his hands held up in a placating gesture. “She’s not wrong,” he admitted, his gaze flickering to Dean. “But it doesn’t change anything. Everything that I told you is still true.”

“You don’t actually believe him?” Ruby cut in, gaze snapping between Sam and Dean.

“I’d believe him before I believe you,” Dean said coolly.

“You can’t be serious, Dean?” Sam demanded. “He’s been lying to you!”

“The less you knew about me the better,” Crowley protested. “Just in case you decided to talk about me to anyone… unsavory.” His gaze flickered to Ruby briefly. “Being Lilith’s right-hand man is what has allowed me to gain the information that I have… and it makes what I am doing with you all the more dangerous.”

“I bet she’s feeding you exactly what information to give them,” Ruby sneered.

“Back off, bitch,” Dean spat. “He’s been helping us. And what exactly have you been doing?”

She turned to him, her expression cold. “I’ve been helping Sam.”

“Yeah, I doubt that.”

“She _has_ been helping me, Dean,” Sam objected.

Dean shook his head as he turned his glare on his brother. “This isn’t helping! She tricked you into using your powers! Do you even know how far off the reservation you've gone? How far from normal? From human?”

“I’m just exorcising demons.”

“With your mind!” he shouted. “What else can you do?”

“I can send them back to hell. It only works with demons, and that's it.”

“But he is getting stronger,” Ruby admitted. “Soon, he’ll be able to kill demons – to kill Lilith. That’s all I’m trying to help him with.”

“I somehow doubt that,” Crowley said softly, taking a step closer to her. “I know how kindly Lilith takes to those who betray her, so I can’t help but be curious how you managed to get out of Hell.”

She looked at him coolly. “She offered me a deal – I’d get out, if I agreed to kill Sam. I took it, then betrayed her.”

He eyed her for a few seconds, then shook his head. “No. Lilith’s not that stupid – she would have known better. And even if she did fall for your ruse, she wouldn’t still be letting to walk. So, what did you really promise her, hm? Why does she need Sam using his powers?”

“Nice try – trying to spin this all around on me, when you’re the one who’s really working for Lilith.”

“That fact that you’re walking around makes no sense.”

“Oh, but it does make sense that Lilith hasn’t realized that her right-hand man has betrayed her?” she scoffed.

“I’m good at keeping up appearances.”

“Clearly. You fooled Dean.”

He smiled bitterly. “I don’t think I could fool Dean, even if I wanted to. He’s a good judge of character – there’s a reason he never fell for your games.”

Ruby shook her head and took a step back, turning to Sam. “Sam, he’s probably been reporting every move you make to Lilith. No wonder we haven’t been able to get close to her, he’s keeping her a step ahead.”

“Don’t listen to her, Sam,” Dean said, stepping up beside Crowley. “She’s just been feeding you lies and making you into whatever Lilith wants you to be.”

“Why would Lilith want him to be able to kill her?” Ruby pointed out. “Because that’s what Crowley told you? Dean, he’s feeding you false information. I have no reason to be loyal to her, but he has been working right along beside her for decades.”

“And it’s grown tiresome,” Crowley said. “I have no loyalty to her, especially when she is dead set on bringing about the end for all of us.” His gaze moved up to rest on Sam. “Sam, I don’t know why Lilith would want you to have these powers, and maybe I’m wrong, maybe she doesn’t. But one way or another, take it from a demon, what you’re doing _is_ dark. It’s evil at its very core.”

Sam shook his head. “I’m saving people. You just don’t like that I’m exorcising demons.”

“I couldn’t care less! I just don’t want to risk Lilith getting what she wants!”

“Sam, don’t you see?” Ruby asked softly. “Lilith is afraid. That’s why she sent him to stop you.”

Suddenly, Ruby screamed as she flew across the room to slam into the wall. Crowley regarded her with narrowed eyes. “If she were really worried, she would be sending demons after _you.”_ His voice was soft and dangerous. “And yet she has made no move against you. Why is that?”

Sam extended his arm out to Crowley, screwing his eyes as he concentrated. It wasn’t hard for Dean to guess what he was doing.

“Sam, don’t!” Dean shouted, lunging forward to grab hold of his arm. But when he looked over his shoulder, Crowley was looking at Sam, unfazed.

“I’m the King of the Crossroads,” he said smoothly. “You’re not strong enough to take me on.”

“Not yet,” Sam spat.

“Sam, you’re seriously taking Ruby’s word on this?” Dean demanded. “He’s helped us stop seals from being broken!”

“So he says. How do we know the places he sent us weren’t just diversions?”

“He gave us the Colt!”

“And yet he hasn’t been able to get us close enough to Lilith – _who he works for –_ to use it!”

“Just because I work for her, it doesn’t mean I have unlimited access to her,” Crowley snapped. “I’d prefer to get you boys close at a time when the chances of you dying are minimal.”

Ruby took advantage of Crowley’s distraction to make a beeline for the door. “Sam, I’m leaving,” she called as she disappeared outside.

Sam turned to look his brother in the eyes. “Are you still siding with Crowley?”

“Yeah, I am,” Dean said firmly.

He sighed. “Then I’m leaving, too.”

“What?” he snapped. “No. Sam, you’re going down a slippery slope, and it's gonna get darker and darker, and god knows where it ends.”

“I’m not gonna let it go too far,” Sam assured as he turned away.

“It’s already gone too far!” He grabbed hold of Sam’s arm again, spinning him back around to face him. “You’re running off with _Ruby!”_

“And you’re sticking with Crowley!” he threw back at him.

“Crowley’s not trying to get me to do anything I shouldn’t be doing.”

“So far as you know.”

“Ruby is turning you into something you shouldn’t be!”

Sam jerked his arm out of Dean’s grip. “If you change your mind, call me. If not, I’ll call you when I’ve killed Lilith.” And with that, he turned and left the room.


	6. Realization

Crowley couldn’t go back to Lilith after all that had transpired. For all they knew, Ruby had told her of his betrayal, and he would be dead the second she caught wind of him.

“I’m surprised you still trust me after that,” Crowley voiced after Dean had effectively downed half his bottle of Scotch.

Dean shrugged. “Always knew you couldn’t have been some run-of-the-mill demon to be able to pull me out of Hell like you did. And you have helped us out – a lot.”

“True.” He poured himself another drink. “But it was hard enough to get you to trust me in the first place… I figured it wouldn’t take much to lose that trust.”

“Nah. You earned my trust against all odds – I figure that means you must be trustworthy.”

“Well, that’s fortunate. Although, with our deal now in place, the consequences of you losing trust in me wouldn’t be quite as terrible. Speaking of which, your part of that deal may be coming into play soon. If Ruby does tell Lilith, she’ll be sending demons after me.”

“And we’ll be ready,” Dean said confidently.

“I sure hope so.” Crowley twisted around to kick his feet up on the bed, leaning back against the headboard, beside Dean.

“Pour me another,” Dean requested, offering his glass out to Crowley.

He arched an eyebrow at the glass, then looked up at Dean. “I think you’ve had enough.”

“With all the shit that’s going on right now between Lilith, Ruby, and Sam – not even close.”

He sighed. “Dean, you can’t drown your sorrows in liquor.”

“Says who?” he challenged.

“Your guardian demon.” He snatched the glass up from Dean’s hand and set it on the table.

Dean snorted. “Cute. But shouldn’t a demon be encouraging drinking – self-destructive coping, and all that?”

“Well, I’m not looking to destroy you completely.” Crowley smirked. “Just a healthy dose of corruption, chipping away at your righteousness,” he teased.

He chuckled. “Not sure I need your help with that. I’m not so righteous, anymore.”

He shrugged. “You don’t give yourself enough credit. You’re a good person, Dean.”

“How can you say that?” Dean looked at him in disbelief. “You _saw_ what I did-”

“Yes, after enduring 30 years of torture. I’ve been on the rack, I know what that’s like. Holding out that long was no small feat.”

He sighed, looking down. “And if I had just held on for 10 more years none of this would be happening.” He shook his head. “It doesn’t matter how long I resisted because I gave in in the end. And…” The words stuck in his throat.

“And a part of you enjoyed it,” Crowley finished for him. “You have a dark side, Dean; that doesn’t make you a bad person. I would know.”

“But how do I live with this?” Dean muttered, his voice barely more than a whisper. “How do I live with what I did?”

“You acknowledge that it was what you had to do to keep going in a terrible situation,” he answered easily. “You take what you learned and you use it to make you stronger.”

He huffed a small laugh as he looked back to Crowley. “You Hell’s shrink, or something?”

“Well, I am in all likelihood out of my job – it wouldn’t hurt to expand my horizons.”

“Well, put a pin in it. We need to focus on getting Lilith first – before Sam does.”

“Agreed. But that’s not happening tonight.” He finished off his drink and the empty glass vanished. “Why don’t you try to get some sleep?”

Dean scoffed. “Yeah, that ain’t happening. I’m gonna need some more of that Scotch to put me out.”

“Might I suggest a mildly healthier sleep aid?”

He arched an eyebrow at him. “What ya’ got for me?”

Crowley smirked. “Well, I’ve found that sex generally leaves humans more susceptible to sleep.”

His eyes went wide, and he could feel his face heating up. “You – you’re suggesting we have sex?” he clarified. No way. Sleeping with Crowley was definitely off the table – there was no way that he was having sex with a demon, no matter how attractive he was, or how much he enjoyed his company, or the fact that kissing him had been like… just no.

“You didn’t see so opposed earlier,” he pointed out. “Besides, you’re wanting to get through to your brother, are you not? Perhaps it would help you to understand – to really _empathize_ with what it’s like to have sex with a demon.”

“Yeah, somehow I don’t see that making much of a difference. That really the best you can come up with?”

He shrugged. “Can’t blame a girl for trying.”

Dean sighed, looking at him curiously. “So, you really want to have sex with me, huh?”

“I have eyes, Dean,” he said as though that made it obvious.

“Right…” he muttered, looking down and trying to block out the part of his mind that was actually considering it.

“What’s the harm in letting yourself have enjoyment for one night?”

“I’ve had many nights of enjoyment,” he protested, looking back up at him. “Hell, just last week I had a great night of enjoyment.”

“Is it really enjoyment when you’re having to hold back a part of yourself, though?”  Crowley angled his body more towards Dean, moving slightly closer. “I know every part of you, Dean – even the parts you hide from little Samantha. You don’t have to pretend with me.”

Dean’s breath caught in his throat. He had wondered vaguely why he felt so relaxed in Crowley’s presence, and that was it – he didn’t have to build up any walls to hide the parts of himself that he was ashamed of. Crowley knew all of him, and yet he was still around, was still able to make the argument that he was a good person.

He didn’t want to look to closely at who initiated the kiss, afraid that if he did, he’d find it was him. Instead, he just enjoyed the slide of their lips against each other and allowed Crowley to push him onto his back. Crowley had been right, Dean needed this – to not have to pretend that he wasn’t on the verge of breaking down, that he had it in him to maintain some modicum of control. For once, he was able to just let go and let Crowley give him what he needed.

It wasn’t just one night of enjoyment, either. No, Crowley couldn’t go back to Lilith, so he stuck with Dean most of the time, and a good portion of their nights were spent, as Crowley would say, helping Dean to unwind a little. That was all it was, though. Just sex. Beyond that, they were working together; there was no attachment, they weren’t even friends with benefits, they were just business partners who liked to fuck. That was all.

“Dean.”

He woke up to Crowley shaking his arm, and as usual, it took him a second to orient himself to where he was. This wasn’t Hell; he was in a nice hotel room, in bed with Crowley. He took a deep breath. “What?” he muttered.

Crowley’s eyebrows were drawn together slightly in concern. “You were… well, you always have nightmares, but this seemed worse.”

Dean shrugged, his face blank. “Some nights are worse than others – it’s not that strange.”

He hesitated for several seconds. “You want to talk about it?”

He squeezed his eyes shut and shook his head. He could see Sam’s bloody face emblazoned on the back of his eyelids, and he was sure that talking about it would only make it worse.

“Alright.” Crowley nodded as Dean opened his eyes again. “How about I go get you some breakfast, then?”

Dean glanced at the clock – it was three in the morning. A little early for breakfast, but he and Crowley both knew that he wasn’t getting back to sleep, so he nodded.

Just a few minutes later, Crowley returned with doughnuts.

“Thanks, man,” Dean said gratefully, giving him a peck on the lips as he took the bag from him. He froze as he realized what he had just done. Their kisses were always heated and carried the implication of sex, they weren’t… that.

Crowley cleared his throat uncomfortably as he took a step back. “I should go,” he announced, not quite looking at Dean. “I have a lead to run down.”

“You need – help?” But Crowley was gone before he even finished the sentence.

Dean sighed as he sank down in a chair. What the hell was going on with him? He knew that Crowley was a demon, and they could never have anything more than what they had now. But he couldn’t deny how great it was to have someone who understood him, who he didn’t feel the need to be perfect for. Crowley accepted him as he was, faults and all, and Dean had never had anything like that before. So yeah, maybe he did want more. But it didn’t make any difference.

When Crowley came back from running down his lead, they fell into bed again and pretended that the kiss had never happened. So, at least Dean hadn’t screwed things up completely. Sex was better than nothing, he had decided, so he’d be keeping his feelings to himself and enjoying the little piece of Crowley he had.


	7. Resolution

“Sam, talk to me, would you?” Dean said to Sam’s voicemail for what felt like the hundredth time. “Demons are coming after Crowley now, and that started right after Ruby found out that he was working with us – hell of a coincidence, don’t you think? Come on, Sammy, can’t you see what she’s doing? Whatever she has up her sleeve ain’t good, and you need to get out.” He hung up with a sigh, and then called Bobby.

“Dean,” Bobby greeted him.

“Hey, Bobby. You heard from Sam?”

“Not a peep. Tell you what I have heard, though – seals are breaking, one right after the other.”

“Dammit,” Dean muttered. “This is all Ruby’s fault. If Crowley was still in with Lilith, we could stop these seals from breaking.”

“Maybe. Don’t make a difference, though. The seals are breaking, and we’re running out of time.” He paused. “You ever think that instead of trying to get Sam to listen to you, you should maybe just suck it up and work together?”

“No way. Not while Ruby’s still in the picture. She’s bad news, Bobby, I’m telling you.”

“But… now, I’m not sayin’ what Sam’s doing is right, but his ability to exorcise demons could be damn useful.”

“Crowley says it’s evil – and I trust a demon to know when something is evil.”

“And you’re sure you’re trusting the right demon, here?” Bobby asked cautiously.

As though he knew the topic of conversation, Crowley suddenly appeared before him, his usual smug expression firmly in place. “Yeah,” Dean answered confidently, looking the demon in the eyes. “I’m sure.”

“Well, I sure hope you’re right. ‘Cause it’s crunch time, and we can’t afford to make mistakes now.”

“I know,” he sighed. “You got anything?”

“Aside from seal after seal being broken? Not a lick.”

“I do,” Crowley spoke up.

Dean’s eyes widened hopefully as he put Bobby on speaker. “What’cha got?”

“For one, I know how Sam’s getting his powers.”

“You’re kidding. How?”

“You aren’t gonna like it,” he warned.

“No shit.”

Crowley sighed. “He’s drinking demon blood.”

Dean just stared at him in disbelief. Because surely Sam wouldn’t… but the way he had been acting, almost like a junkie…. He was, wasn’t he?

“Damn,” Bobby muttered. “How’d you learn that?”

“I did some research into Azazel’s work – thought it could be useful.”

“And you’re sure that’s what’s going on?” Dean checked.

“Sorry, Dean. And it gets worse.”

“Course it does.”

“The amount of blood he would need to kill Lilith _will_ change him, even more than it’s already tainting him.”

“I sure hope you have some good news to follow this with,” Bobby said.

“As a matter of fact…” Crowley grinned. “Lilith’s getting close to the end. She’s slowing down, and that could be the break we need to catch up with her.”

“Great.” Dean went straight for the hotel room safe and got out the Colt. “Let’s go.”

Following demonic signs led them to Ilchester, Maryland, but they still had no idea where in Ilchester Lilith would be. So, they dove into research.

“Crowley,” Dean said urgently after about an hour of research. “I think I know where Lilith is. St. Mary’s Convent – abandoned in ’72 after a priest got possessed by a demon and disemboweled eight nuns – a demon by the name of Azazel.”

“Could be the location of the final seal,” Crowley agreed, but a frown was forming on his face. “Which would mean that Azazel set this plan in the works over three decades ago…. And then he made Sam into what he is. That’s not a coincidence.”

“You think Sam’s involved in breaking the seals?” he asked as he got up and gathered his things.

“Azazel didn’t do anything without a purpose,” he said as he came to Dean’s side. “Why would he give Sam these powers, otherwise? Why would Ruby be teaching him to use them?”

“Well, it sure as hell isn’t to kill Lilith.”

Crowley froze. “What if it is?” he asked softly.

Dean looked at him incredulously. “What?”

“Lilith was the first demon – what if the final seal is a sacrifice?”

“For Sam to kill Lilith?” Dean’s heart was pounding. Dammit. They _really_ needed to get to Lilith before Sam did.

“The universe has a funny way of balancing things out – you broke the first seal; your brother breaks the last.”

He snatched up his phone and called Sam. “Sam, please listen to me. We think we figured out the final seal – it’s you killing Lilith. Please, Sam. I’m closing in on her. Let me do it.” He shoved his phone in his pocket and turned to Crowley. “We need to get to that convent _now.”_

Crowley snapped his fingers and they were outside St. Mary’s, standing right beside a car parked in the parking lot. Dammit, Sam was already there.

Dean turned and broke off running into the convent, Crowley right behind him. He turned a corner and he could see into the sanctuary, could see Sam and Ruby standing in front of Lilith with Sam’s arm outstretched towards her. Ruby looked back at Dean and smiled, then she raised a hand and the door slammed shut. But Crowley turned the corner right behind him, and with a wave of his hand, the door flung open again.

“Sam, stop!” Dean shouted as he ran into the room, raising the Colt. Ruby took a step forward, but with another flick of Crowley’s wrist, she was thrown against the wall.

Sam turned to him in confusion. “Dean?”

Dean aimed the gun at Lilith’s head and pulled the trigger. He held his breath as the bullet spiraled towards her and buried itself in her forehead. She flickered with light, then went limp, and Dean breathed out a sigh of relief.

“NO!” Ruby shouted as she hurtled herself at Dean. He dropped the Colt as her hand wrapped around his throat and she pinned him to the wall. “Do you have _any_ idea how much work I-” She cut off abruptly as she flickered and dropped to the ground, revealing Crowley standing behind her, holding the Colt.

Dean gasped for breath as he nodded to Crowley. “Thanks.”

“Don’t mention it.” He handed the gun back to Dean.

“Dean, wha-what…?” Sam’s bewildered voice drew his attention.

“Sam,” Dean said gently, taking a step towards him as he slid the Colt into his pocket. “The final seal was you killing Lilith… it’s been Ruby’s plan all along.” There was no longer any doubt about it – Ruby’s reaction confirmed that Crowley was right about the final seal.

Sam deflated, his eyes going wide in horror. “I… I almost…” He took a shaky breath.

“Hey, you _didn’t,”_ he said firmly, taking another step forward and placing his hand on Sam’s shoulder. “It’s okay, Sammy.” He pulled him into a tight hug. “It’s okay.” He felt Sam slump into his arms, defeated and shaking slightly. He just held him in silence until the shaking died down and he felt that Sam would be alright if he let go. Slowly, he removed his arms from around him and took a step back.

Crowley cleared his throat. “Not to ruin the moment, but Sam is still chock full of demon blood.”

Dean glanced at Sam before nodding to Crowley. “I know. We’ll deal.” He turned back to his brother. “You’ll get clean, right, Sammy?”

Sam nodded without looking at either of them. “Yeah,” he muttered, his voice rough with emotion.

“I know you will,” Dean encouraged. “Cause you’re stronger than this.”

“Well, then.” Crowley clapped his hands together. “I suppose that’s everything – Apocalypse averted, Lilith dead, happily ever after for everyone.”

Dean couldn’t stop the slight frown as he turned back to him. “You’re leaving.”

He shrugged. “No point in sticking around. It’s been fun, but time to get back to my day job.”

He swallowed around the lump in his throat. This really shouldn’t be hitting him so hard. He had always known that things between himself and Crowley was a short-term arrangement, but he still didn’t want to see him go for good. “You sure demons won’t be targeting you?”

Crowley smirked. “You worried about me, squirrel?”

A pink tinge appeared on his cheeks. “I was just checkin’.”

He chuckled. “I should be fine. If not, I know who to call.”

Dean nodded. “Well… thanks for everything.”

The smile that he got in return was almost genuine. “You too, Dean.” A second later, he was gone.


	8. Return

It took some time for things to return to normal for Sam and Dean – well, as close to normal as things would ever be for them. But Sam got clean of demon blood, he and Dean repaired their relationship, and they got back to hunting. It was their normal.

Dean still missed Crowley, though. Even while he had realized that he was falling for Crowley a little bit, he hadn’t realized just how much until he was out of his life. He wished he could still talk to him about everything he was struggling with. It wasn’t as though he couldn’t talk to Sam, it was just that Crowley understood more, and always seemed to know just what to say. Either that, or he knew how to get his mind off his problems more effectively than anyone else. There was just something about Crowley – Dean clicked with him in a way that he had never clicked with anyone before. It was just his luck that he would fall hard for a demon who had no hope of returning his feelings. He just had to come to terms with the fact that Crowley was out of his life for good.

If only other demons were staying out of his life, too, he thought as he glared at the black-eyed bastard that had him and Sam pinned against the wall.

“Hmm… I think I’m going to start with you, Dean,” the demon said casually, as though he was deciding what to have for dinner. Hell, maybe he was; there was no telling with demons. “And make your little brother watch. How does that sound?”

“Weird,” Dean said matter-of-factly. “Sam and I are brothers – we’re not really into voyeurism, especially not with each other. Besides, you’re not my type.”

“Cute,” he sneered. “But-”

“What. The. _Hell._ Do you think you’re doing?” a very familiar voice suddenly spoke from behind the demon, whose eyes went wide as he looked over his shoulder at the new arrival.

“Sir! I-”

“I do believe I issued the command that Sam and Dean are _off limits,_ did I not?” Crowley demanded as he stepped closer to the other demon.

“W-Well, yes, but they-”

“Don’t care.” He snapped his fingers and the demon vanished in a puff of smoke, Sam and Dean sliding to the floor as his hold on them broke. The smoke cleared, and Crowley smirked at Sam and Dean as they came into view. “Hello boys.”

“Crowley,” Dean huffed, the corners of his lips turning up. “Damn, it’s good to see you.”

His eyes ran over Dean’s form, and he smiled. “You too.”

“Uh, not that I’m not grateful,” Sam said. “But… what was that all about?”

“Oh, I’m King of Hell now,” he said casually.

Dean blinked in surprise. “What?”

Sam huffed a laugh. “So, that’s what you really wanted out of killing Lilith, huh?” His tone wasn’t accusing, just matter-of-fact.

Crowley’s eyes widened innocently. “Not at all. This was just a happy accident. Next in line didn’t want the throne, so someone had to step up.”

“Well, I suppose that’s better than having demons running you down for helping to kill Lilith,” Dean said. “Congratulations.”

“Thank you.”

“But, uh, what was that you said about Sam and me being off limits?”

“Oh, I ordered all demons not to harm you two,” he said with a shrug.

“Why?” Sam asked, his eyebrows furrowing in confusion.

“Not for your sake, moose, I assure you.” His eyes flickered to him briefly before resting once again on Dean.

Dean cleared his throat, getting the picture. “Thanks, Crowley. Really.”

“Of course.” He sighed sadly as he looked down. “Well, I suppose I should be going.”

Dean hesitated, but what was really the point in holding back anymore? He’d probably never be seeing Crowley again one way or the other, so he might as well get it off his chest. “Wait.” Crowley looked at him with raised eyebrows, and he bit his lip as he turned to Sam. “Could you give us a minute?”

Sam’s eyebrows shot almost up to his hairline. “…Sure…” He glanced between the two of them as he walked out of the room.

“What is this about?” Crowley asked cautiously a few seconds after Sam had left the room.

Dean took a deep breath. “I miss you.”

He blinked. “Where is this going, Dean?” he asked slowly.

“So, you don’t miss me?” Dean asked, taking a step forward. “At all?”

His eyes narrowed. “What kind of question is that?”

“A simple one.” His calm voice was at odds with the pounding in his chest.

“No, it’s not,” Crowley disagreed, his eyes fixed on the wall behind Dean. “If I say yes, that means you mean something to me. And if you mean something to me, then that will lead to more questions that have progressively more complicated answers.”

“So, if you say no?” Dean pressed.

He met his gaze. “Then I hurt you.” He took a deep breath. “And I don’t know which outcome is worse.”

He gave a tentative smile. “You know, you kinda as good as answered the question.”

“I know,” he sighed. “But that doesn’t mean I can’t pretend.”

“And who exactly does that make things better for, Crowley?” he demanded.

“Both of us. I’m the King of Hell – I don’t do relationships.”

“I never said anything about a relationship,” Dean argued, even though a part of him ached at those words.

“You will,” Crowley countered confidently. “But nothing can come of this conversation, Dean, so what’s the point in having it?”

Dean was about to back down, to say that Crowley was right, but then a new wave a resolve came over him. He set his jaw, taking another step closer. “Because this is bullshit, Crowley. We both want the same thing here, so why can’t we have it? I have had to let go of so many things in my life that I had no control over, but we have control over this. We don’t have to give it up as a lost cause before ever even try. And maybe you’re right – maybe it is hopeless. But I’ve defied the odds before, so maybe I will again. We don’t know anything unless we try.”

Crowley eyed him appraisingly for several seconds. “I’m not giving up Hell for you,” he finally said.

“I ain’t askin’ you to.”

He nodded thoughtfully. “You don’t think your brother will feel betrayed? After everything that happened between him and Ruby?”

“We got out of that mess because of you. He’ll deal.”

He squinted at him as he continued to mull it over. “I’ll have to tell the demons that I’m using you,” he finally said decidedly. “Can’t have them thinking I’m soft on a Winchester.”

Dean’s face split into a smile. “Course not.”

He met his eyes with a grin. “I suppose I should take you on a date, or something.”

“I could go for that.”

“You should probably talk to your brother first, though – assuming he hasn’t been eavesdropping on this entire conversation.”

Dean nodded. “I’ll be right back.” He made to walk past Crowley, to the door, but Crowley grabbed him by his jacket and pulled him into a kiss. Yeah, it was definitely worth giving this a shot.


End file.
